Work

Approaches to Polycyclic 1,4-Dioxygenated Xanthones. Application to Total Synthesis of the Aglycone of IB-00208

Year: 2014

Type: article

Abstract: Hexacyclic xanthone natural products such as IB-00208 present a formidable challenge in organic synthesis. A new approach to polycyclic 1,4-dioxygenated xanthones from benzocyclobutenones has been developed and applied to the first total synthesis of the aglycone of IB-00208. The 22-step synthesis features an acetylide stitching process that joins an aryl aldehyde with an angularly fused benzocyclobutenone, which was prepared by a ring-closing metathesis reaction. The resulting acetylenic benzocyclobutenone diol underwent a Moore rearrangement to give an intermediate that was further elaborated to the aglycone of IB-00208 as a mixture of hydroquinone-quinone tautomers.

Source: Organic Letters

DOI: 10.1021/ol503336t

Authors: Jingyue Yang, Daniel Knueppel, Bo Cheng, Douglas Mans, Stephen F. Martin

Institution: The University of Texas at Austin

Language: English

Topic: Synthesis of Organic Compounds

Subfield: Pharmacology (medical)

Field: Medicine

Domain: Health Sciences

Open Access status: hybrid

Estimated APC paid: $4,500